14
1 General Introduction
acid crystals. Angew Chem Int Ed 54:4815–4817. (m) Naumov P, Bharadwaj PK (2015) Singlecrystal-to-single-crystal transformations. CrystEngComm 17:8775. (n) Chaudhary A, Mohammad A, Mobin S M (2017) Recent advances in single-crystal-to-single-crystal transformation
at the discrete molecular level. Cryst Growth Des 17:2893–2910
12. Grein F (2002) Twist angles and rotational energy barriers of biphenyl and substituted biphenyls.
J Phys Chem A 106:3823–3827
13. Flack HD (2003) Chiral and achiral crystal structures. Helv Chemica Acta 86:905–921
14. (a) Wallach O (1895) Zur Kenntniss der Terpene und der ätherischen Oele. Liebigs Ann Chem
286:90–118. (b) Brock CP, Schweizer WB, Dunitz JD (1991) On the validity of Wallach’s
rule: on the density and stability of racemic crystals compared with their chiral counterparts.
J Am Chem Soc 113:9811–9820. (c) Marciniak J, Michal A, Weizhao C, Andrzej K (2014)
Wallach’s rule enforced by pressure in mandelic acid. J Phys Chem C 118:4309–4313
15. (a) Vogelsberg CS, Garcia-Garibay MA (2012) Crystalline molecular machines: function, phase
order, dimensionality, and composition. Chem Soc Rev 41:1892–1910. (b) Khuong TAV, Nuñez
JE, Godinez CE, Garcia-Garibay MA (2006) Crystalline molecular machines: a quest toward
solid-state dynamics and function. Acc Chem Res 39:413–422
16. (a) Comotti A, Bracco S, Valsesia P, Beretta M, Sozzani P (2010) Fast molecular rotor dynamics
modulated by guest inclusion in a highly organized nanoporous organosilica. Angew Chem Int
Ed 49:1760–1764. (b) Bracco S, Comotti A, Valsesia P, Chmelka BF, Sozzani P (2008) Molecular rotors in hierarchically ordered mesoporous organosilica frameworks. Chem Commun
39:4798–4800
17. (a) Kitagawa S, Kitaura R, Noro S -I (2004) Functional porous coordination polymers. Angew
Chem Int Ed 43:2334–2375. (b) Inukai M, Fukushima T, Hijikata Y, Ogiwara N, Horike S,
Kitagawa S (2015) Control of molecular rotor rotational frequencies in porous coordination
polymers using a solid-solution approach. J Am Chem Soc 137:12183–12186. (c) Seo J, Matsuda R, Sakamoto H, Bonneau C, Kitagawa S (2009) A pillared-layer coordination polymer with
a rotatable pillar acting as a molecular gate for guest molecules. J Am Chem Soc 131:12792–
12800. (d) Horike S, Matsuda R, Tanaka D, Matsubara S, Mizuno M, Endo K, Kitagawa S
(2006) Dynamic motion of building blocks in porous coordination polymers. Angew Chem Int
Ed 45:7226–7230
18. (a) Dominguez Z, Khuong TAV, Sanrame CN, Dang H, Nuñez JE, Garcia-Garibay MA (2003)
Molecular compasses and gyroscopes with polar rotors: synthesis and characterization of
crystalline forms. J Am Chem Soc 125:8827–8837. (b) Horansky RD, Clarke LI, Winston EB,
Price JC, Karlen SD, Jarowski PD, Santillan R, Garcia-Garibay MA (2006) Dipolar rotor-rotor
interactions in a difluorobenzene molecular rotor crystal. Phys Rev B 74:54306. (c) Akutagawa
T, Koshinaka H, Sato D, Takeda S, Noro S-I, Takahashi H, Kumai R, Tokura Y, Nakamura T
(2009) Ferroelectricity and polarity control in solid-state flip-flop supramolecular rotators. Nat
Mater 8:342–347. (d) Setaka W, Yamaguchi K (2013) Order–disorder transition of dipolar rotor
in a crystalline molecular gyrotop and its optical change. J Am Chem Soc 135:14560–14563
19. Bracco S, Beretta M, Cattaneo A, Comotti A, Falqui A, Zhao K, Rogers C, Sozzani P (2015)
Dipolar rotors orderly aligned in mesoporous fluorinated organosilica architectures. Angew
Chem Int Ed 54:4773–4777
20. (a) Winston EB, Lowell PJ, Vacek J, Chocholoušová J, Michl J, Price JC (2008) Dipolar molecular rotors in the metal–organic framework crystal IRMOF-2. Phys Chem Chem Phys 10:5188–
5191. (b) Devautour-Vinot SB, Maurin G, Serre C, Horcajada P, Da Cunha DP, Guillerm V,
De Souza Cosa E, Taulelle F, Martineau C (2012) Structure and dynamics of the functionalized MOF type UiO-66(Zr): NMR and dielectric relaxation spectroscopies coupled with DFT
calculations. Chem Mater 24:2168–2177
21. Hughs M, Jimenez M, Khan SI, Garcia-Garibay MA (2013) Synthesis, rotational dynamics,
and photophysical characterization of a crystalline linearly conjugated phenylene ethynylene
molecular dirotor. J Org Chem 78:5293–5302
1 General Introduction
acid crystals. Angew Chem Int Ed 54:4815–4817. (m) Naumov P, Bharadwaj PK (2015) Singlecrystal-to-single-crystal transformations. CrystEngComm 17:8775. (n) Chaudhary A, Mohammad A, Mobin S M (2017) Recent advances in single-crystal-to-single-crystal transformation
at the discrete molecular level. Cryst Growth Des 17:2893–2910
12. Grein F (2002) Twist angles and rotational energy barriers of biphenyl and substituted biphenyls.
J Phys Chem A 106:3823–3827
13. Flack HD (2003) Chiral and achiral crystal structures. Helv Chemica Acta 86:905–921
14. (a) Wallach O (1895) Zur Kenntniss der Terpene und der ätherischen Oele. Liebigs Ann Chem
286:90–118. (b) Brock CP, Schweizer WB, Dunitz JD (1991) On the validity of Wallach’s
rule: on the density and stability of racemic crystals compared with their chiral counterparts.
J Am Chem Soc 113:9811–9820. (c) Marciniak J, Michal A, Weizhao C, Andrzej K (2014)
Wallach’s rule enforced by pressure in mandelic acid. J Phys Chem C 118:4309–4313
15. (a) Vogelsberg CS, Garcia-Garibay MA (2012) Crystalline molecular machines: function, phase
order, dimensionality, and composition. Chem Soc Rev 41:1892–1910. (b) Khuong TAV, Nuñez
JE, Godinez CE, Garcia-Garibay MA (2006) Crystalline molecular machines: a quest toward
solid-state dynamics and function. Acc Chem Res 39:413–422
16. (a) Comotti A, Bracco S, Valsesia P, Beretta M, Sozzani P (2010) Fast molecular rotor dynamics
modulated by guest inclusion in a highly organized nanoporous organosilica. Angew Chem Int
Ed 49:1760–1764. (b) Bracco S, Comotti A, Valsesia P, Chmelka BF, Sozzani P (2008) Molecular rotors in hierarchically ordered mesoporous organosilica frameworks. Chem Commun
39:4798–4800
17. (a) Kitagawa S, Kitaura R, Noro S -I (2004) Functional porous coordination polymers. Angew
Chem Int Ed 43:2334–2375. (b) Inukai M, Fukushima T, Hijikata Y, Ogiwara N, Horike S,
Kitagawa S (2015) Control of molecular rotor rotational frequencies in porous coordination
polymers using a solid-solution approach. J Am Chem Soc 137:12183–12186. (c) Seo J, Matsuda R, Sakamoto H, Bonneau C, Kitagawa S (2009) A pillared-layer coordination polymer with
a rotatable pillar acting as a molecular gate for guest molecules. J Am Chem Soc 131:12792–
12800. (d) Horike S, Matsuda R, Tanaka D, Matsubara S, Mizuno M, Endo K, Kitagawa S
(2006) Dynamic motion of building blocks in porous coordination polymers. Angew Chem Int
Ed 45:7226–7230
18. (a) Dominguez Z, Khuong TAV, Sanrame CN, Dang H, Nuñez JE, Garcia-Garibay MA (2003)
Molecular compasses and gyroscopes with polar rotors: synthesis and characterization of
crystalline forms. J Am Chem Soc 125:8827–8837. (b) Horansky RD, Clarke LI, Winston EB,
Price JC, Karlen SD, Jarowski PD, Santillan R, Garcia-Garibay MA (2006) Dipolar rotor-rotor
interactions in a difluorobenzene molecular rotor crystal. Phys Rev B 74:54306. (c) Akutagawa
T, Koshinaka H, Sato D, Takeda S, Noro S-I, Takahashi H, Kumai R, Tokura Y, Nakamura T
(2009) Ferroelectricity and polarity control in solid-state flip-flop supramolecular rotators. Nat
Mater 8:342–347. (d) Setaka W, Yamaguchi K (2013) Order–disorder transition of dipolar rotor
in a crystalline molecular gyrotop and its optical change. J Am Chem Soc 135:14560–14563
19. Bracco S, Beretta M, Cattaneo A, Comotti A, Falqui A, Zhao K, Rogers C, Sozzani P (2015)
Dipolar rotors orderly aligned in mesoporous fluorinated organosilica architectures. Angew
Chem Int Ed 54:4773–4777
20. (a) Winston EB, Lowell PJ, Vacek J, Chocholoušová J, Michl J, Price JC (2008) Dipolar molecular rotors in the metal–organic framework crystal IRMOF-2. Phys Chem Chem Phys 10:5188–
5191. (b) Devautour-Vinot SB, Maurin G, Serre C, Horcajada P, Da Cunha DP, Guillerm V,
De Souza Cosa E, Taulelle F, Martineau C (2012) Structure and dynamics of the functionalized MOF type UiO-66(Zr): NMR and dielectric relaxation spectroscopies coupled with DFT
calculations. Chem Mater 24:2168–2177
21. Hughs M, Jimenez M, Khan SI, Garcia-Garibay MA (2013) Synthesis, rotational dynamics,
and photophysical characterization of a crystalline linearly conjugated phenylene ethynylene
molecular dirotor. J Org Chem 78:5293–5302